Tag: M.W=100-200

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H8N2

[00641] A mixture of Example 134b (100 mg, 0.235 mmol), Example 134c (108 mg, 1.0 mmol), K2C03 (162 mg, 1.175 mmol), Cul (11 mg, 0.058 mmol) in dry DMSO (2 mL) was heated at 125¡ãC for 24 h. The reaction was cooled to r.t., and water (25 mL) was added. The resulting mixture was stirred for 5 min, and filtered to give the crude product, which was purified by prep-HPLC (by Ultimate XB-C18, 50 x 250 mm, 10 muetaiota, speed: 80 mL/min, eluent: A/B = H20/CH3C = from 75/25 to 45/55 over 30 min. Ret. Time =: 24.94 min), followed by prep-TLC (DCM/MeOH = 10/1) to give the desired product Example 134 (1.2 mg, yield 1percent) as a white solid. LC-MS [M+l]+ = 454.0. NMR (400 MHz, Chloroform-d) delta 11.80 (s, 1H), 8.23-8.15 (m, 3H), 8.04 (s, 1H), 7.97 (t, J= 7.9 Hz, 1H), 7.83 (s, 1H), 7.50 (s, 2H), 7.12 (s, 1H), 4.83 (t, J= 8.9 Hz, 1H), 4.58 (s, 2H), 4.41 (t, J= 6.9 Hz, 1H), 3.81 (s, 2H), 2.88 (s, 2H), 1.96 (d, J= 38.7 Hz, 1H), 0.89 (d, J= 7.0 Hz, 2H), 0.83 (s, 2H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (214 pag.)WO2019/51265; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1849-02-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1849-02-1, name is 2-Chloro-1-methyl-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 2 0.43 g (5.0 mmol) of piperazine and 0.24 g (1.0 mmol) of the compound obtained in Step 1 were placed in a dried round flask provided with nitrogen gas, followed by reacting the mixture at 150C for 30 mins. After cooling to room temperature, the reaction mixture was acidified with IN-HCl solution and washed with dichloromethane. The water layer was treated with IN-NaOH solution and extracted with dichloromethane. The formed organic layer was dried over anhydrous magnesium sulfate and concentrated under a reduced pressure, and the resulting residue was subjected to silica gel column chromatography (dichloromethaneimethanol^il) to obtain 0.15 g of l-methyl-2-(piperazin-l-yl)-benzoimidazole (yield: 69%).

The synthetic route of 2-Chloro-1-methyl-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; CHEMON INC.; WO2008/153325; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 45676-04-8, name is 1-tert-Butylimidazole, A new synthetic method of this compound is introduced below., Product Details of 45676-04-8

THF (200 ml) and 1-tert-butylimidazole (12.42 g, 0.1 mol) were added into a 500 ml reactor containing a stirrer with N2 fully charged. After stirring evenly, the solution was cooled to -45 C. A solution of n-butyl lithium hexane (41.6 ml, 2.4 mol/L) was extracted with a 100 mL syringe and added slowly to the solution above while string. After stirring at -45 C. for 1 hour, the solution was raised to room temperature and kept stirring for 1 hour. Then, the solvent was removed by vacuum, and hexane (100 ml) was added in. 12.08 g (0.098 mol, 92.8%) product was obtained by remove the volatile components in vacuum after dispersion and filtration.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Tianjin University of Science&Technology; Jiang, Tao; Chen, Yanhui; Zhang, Le; Alam, Fakhre; Shao, Huaiqi; Li, Jian; Yan, Bing; (9 pag.)US2019/106366; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 15965-31-8, name is 5-Chloro-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 5-Chloro-1H-imidazole

To a stirred mixture of intermediate E(3) (4.0 g, 11.1 mmol), KOH (0.93 g, 16.6 mmol) in DMSO (30 mL) was added chloroimmidazole (1.69 g, 16.6 mmol) at room temperature. The reaction mixture was stirred at 90 C for 18 h while monitoring by LC-MS and TLC. The reaction mixture was poured into crushed ice (50 g) and extracted with ethyl acetate (3 x 200 mL). The organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude compound was purified by column chromatography (60-120 mesh silica) using 60-70% ethyl acetate in pet-ether to give tert-butyl 2-(2-(2-(4-chloro-lH-imidazol-l-yl)-5- nitrophenoxy)ethoxy)ethylcarbamate ( 3.0 g, 63.29%) as a yellow solid. LC-MS (M- 100)+ = 326.2. 1H NMR (400 MHz, CDC13) delta ppm 8.01-7.97 (2H, m), 7.88 (1H, s), 7.46- 7.44 (1H, d, J=8.8 Hz), 7.28-7.27 (1H, m), 4.92 (1H, s), 4.34-4.33 (2H, m), 3.86-3.83 (2H, m), 3.59-3.57 (2H, t, J=5.2 Hz), 3.37-3.34 (2H, m), 1.43 (9H, s).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 15965-31-8.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BOY, Kenneth M.; GUERNON, Jason M.; MACOR, John E.; THOMPSON III, Lorin A.; WU, Yong-Jin; ZHANG, Yunhui; WO2012/9309; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 68282-53-1, A common heterocyclic compound, 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

COMPOUND 12.1. 31: 4-({6,7-DIMETHOXY-2-[(4-METHYL-1H-IMIDAZOL-5- YL)METHYL]-1,2,3,4-TETRAHYDROISOQUINOLIN-1-YL}METHOXY)-N,N- DIETHYLBENZAMIDE; To a solution of INTERMEDIATE 5. 1. 1 (0.2 mg, 0.5 mmole) and 4-methyl-5- imidazolecarboxaldehyde (0.06 g, 0.6 mmole) in 1,2-dichloromethane (5 mL) was added sodium triacetoxyborohydriden (0.32 g, 1.5 mmole) and the resulting solution was stirred at room temperature for 18 h. Sodium hydroxide (1M, 20 mL) and chloroform (60 mL) was added and the mixture filtered through a Whatman IPS filter paper. The solvent was removed from the organic phase in vacuo and the residue purified by flash chromatography (2/98 Methanol/Chloroform) to give COMPOUND 12.1. 31 (0.06 g, 25%) as a yellow amorphous solid. 1H NMR (500 MHz, CDC13) : No. 1.17 (br s, 6 H), 2.14 (s, 3H), 2.56 (dd, J4,14. 5 Hz, 1H), 3.83 (m, 2H), 3.84 (s, 3H), 3.86 (s, 3H), 4.03 (app q, J 5 Hz, 2H), 4.27 (app t, J 10 Hz, 1H), 5.95 (br s, 1H), 6.62 (s, 1H), 6.67 (s, 1H), 6.87 (d, J 9 Hz, 2H), 7.31 (d, J9 Hz, 2H), 7.49 (s, 1H). 13C NMR (125 MHz, CDC13) : i5ll. 28,24. 22,44. 38,48. 34,55. 86,56. 01,59. 20,71. 59, 111. 14, 111. 56, 114. 30, 125.38, 125.64, 127.12, 128. 18, 129.78, 130.76, 132.99, 147.53, 148. 17,159. 27,171. 15. (+) LRESIMS mlz 493 [M+H] +.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 4532-96-1, The chemical industry reduces the impact on the environment during synthesis 4532-96-1, name is 1-Isopropyl-1H-imidazole, I believe this compound will play a more active role in future production and life.

A) 1,1′-Diisopropyl-3,3′-methylenediimidazolium dibromide 8 0.009 mol of dibromomethane (1.564 g; 0.63 ml) and 5 ml of tetrahydrofuran are added to 0.018 mol of isopropylimidazole 1 (2.000 g) in an ACE pressure tube. The reaction mixture is stirred at 80 C. for 20 hours. The solid which precipitates is washed repeatedly with a little tetrahydrofuran. A white solid 8 is obtained. Empirical formula: C13H22N4Br2 M=394.154 g/mol Yield: 1.032 g (36.7% of theory) Melting point: decomposition at >172 C. 1H (ppm, d6-DMSO, 300.13 MHz): delta=9.68 (s, 2H, NCN); 8.11 (t, 2H, J=1.75 Hz, NCCHN); 8.04 (t, 2H, J=1.75 Hz, NCHCN); 6.66 (s, 2H, NC2N); 4.70 (sept, 2H, J=6.6 Hz (CH3)2CN); 1.50 (d, 12H, J=6.6 Hz, C3 group)

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Isopropyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BASF SE; TECHNISCHE UNIVERSITAET DRESDEN; US2009/326237; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 167487-83-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 167487-83-4, name is Ethyl 1H-benzo[d]imidazole-7-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Into a 100-mL round-bottom flask was placed a suspension of sodium hydride (1.24 g, 31.00 mmol, 1.20 equiv) in DMF (10 mL). Ethyl 1H-1,3-benzodiazole-4-carboxylate (4.9 g, 25.76 mmol, 1.00 equiv) was added to the reaction solution at 0 C. The resulting solution was stirred for 1 h at 0 C. Next, iodomethane (3.66 g, 25.79 mmol, 1.00 equiv) was added to the reaction mixture at 0 C. The resulting solution was allowed to react, with stirring, for an additional 2 h while the reaction mixture temperature was maintained 0 C in an ice bath. Then, the reaction was quenched by the addition of 100 mL of water. The resulting solution was extracted with 3×200 mL of dichloromethane. The combined organic layers were washed with 3×200 mL of H2O. The resulting mixture was concentrated under vacuum and the resulting residue was purified by silica gel column with dichloromethane/methanol (97:3) as eluent to furnish 2.4 g (46%) of ethyl 1-methyl-1H-1,3-benzodiazole-4-carboxylate as a red solid.

The synthetic route of Ethyl 1H-benzo[d]imidazole-7-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LYCERA CORPORATION; AICHER, Thomas, Daniel; PADILLA, Fernando; TOOGOOD, Peter, L.; CHEN, Shoujun; (331 pag.)WO2016/138335; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 124312-73-8, These common heterocyclic compound, 124312-73-8, name is (1-Methyl-1H-imidazol-2-yl)methanamine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

EXAMPLE 13 To a solution of ester (750 mg, 1.83 mmol), (1-methyl-1H-imidazol-2-yl)methanamine (0.50 mL, 4.50 mmol) and DBU (0.80 mL, 5.35 mmol) in DCM (50 mL) was added AlCl3 (750 mg, 5.62 mmol). The reaction mixture was stirred at rt for 3 h. The reaction was diluted with DCM (200 mL) and 3N NaOH (100 mL) and stirred for 10 min. The layers were separated and the organic layer was washed with H2O (2¡Á100 mL), brine (100 mL), and dried over Na2SO4. The solvent was removed under reduced pressure and the reaction crude was purified on silica column (0-5% MeOH/DCM) to yield the desired product as a white solid (275 mg, 32%). 1H NMR (CDCl3) delta: 11.0 (t, 1H), 9.45 (d, 1H), 8.61 (d, 1H), 7.76 (dd, 1H), 7.50 (m, 1H), 7.45 (m, 1H), 6.99 (d, 1H), 6.90 (d, 1H), 6.83 (d, 1H), 4.82 (d, 2H), 3.93 (t, 4H), 3.81 (t, 4H), 3.70 (s, 3H). LCMS (ES): m/z 475 [M+1]+.

The synthetic route of 124312-73-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NAGASAWA, Johnny Yasuo; PIERRE, Fabrice; HADDACH, Mustapha; SCHWAEBE, Michael; DARJANIA, Levan; WHITTEN, Jeffrey P.; US2009/93455; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 5-Methyl-1H-imidazole-4-carbaldehyde

To a solution of 4-methyl-lH-imidazole-5-carbaldehyde (5.0 g, 45.4 mmol) in anhydrous THF (5OmL) was added diaza(l,3)bicyclo[5.4.0]undecane (DBU, 6.8 mL, 45.4 mmol) and 2-iodopropane (4.5 mL, 45.4 mmol). The reaction mixture was stirred at room temperature overnight. Water (50 mL) was added. The mixture was extracted with EtOAc (1 x 50 mL) and 2-butanol (2 x 50 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo. The crude product was purified by flash chromatography (0-2% MeOH/DCM), affording 4-methyl-l-(propan-2-yl)-lH-imidazole-5-carbaldehyde (691 mg, 10% yield).

The synthetic route of 68282-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHLORION PHARMA, INC.; UNIVERSITE LAVAL; ATTARDO, Giorgio; TRIPATHY, Sasmita; WO2010/132999; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1849-01-0, name is 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 1849-01-0

Example 37; Preparation of Intermediate Compound 37A; To a solution of 2-bromo-4-carbomethoxythiazole (1.5 g, 6.78 mmol) in dioxane (80 mL) at room temperature was added 1 -methyl-2-benzimidazolone (1.0 g, 6.78 mmol) followed by CuI (0.13 g, 0.68 mmol), K2CO3 (1.0 g, 7.47 mmol), trans- N, lambda/-dimethylcyclohexane (0.21 mL, 1.35 mmol). The mixture was degassed under house vacuum and filled with N2 six times and heated to 90 C. The mixture was stirred for 12 hours, cooled to rt, and concentrated under reduced pressure. The EPO crude product was purified using flash chromatography using a 20:1 mixture of CH2CVMeOH to provide 1.8 g (92% yield) of the title compound as an off-white solid. LC-MS [M+H] = 290.2; 98% purity.

The synthetic route of 1849-01-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2008/54749; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem